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Reactions of doubly deprotonated 2,6-naphthalenedicarboxylic acid with alcohols: Proton transfer versus solvation
, Article International Journal of Mass Spectrometry ; 2016 ; 13873806 (ISSN) ; Meyer, M. M ; O'Hair, R. A. J ; Fattahi, A ; Schmidt, J ; Kass, S. R ; Sharif University of Technology
Elsevier B.V
2016
Abstract
Electrospray ionization of 2,6-naphthalenedicarboxylic acid readily affords its doubly deprotonated dicarboxylate dianion (1 2-). This species clusters with background water and added alcohols in an ion trap at ∼10-3 Torr. Sequential solvation is observed to afford mono and dicoordinated ions. Surprisingly, the latter cluster (1 2- • 2TFE) is protonated by 2,2,2-trifluoroethanol (TFE) whereas 1 2-and 1 2- • TFE are not even though δHacid(TFE)=361.7±2.5kcalmol-1 (as given in the NIST website at http://webbook.nist.gov) and the B3LYP/6-31+G(d,p) proton affinities are 384.7 (1 2-), 377.6 (1 2- • TFE), and 362.7 (1 2- • 2TFE) kcal mol-1. That is, only the weakest base in this series, and the...
Reactions of doubly deprotonated 2,6-naphthalenedicarboxylic acid with alcohols: Proton transfer versus solvation
, Article International Journal of Mass Spectrometry ; Volume 418 , 2017 , Pages 180-187 ; 13873806 (ISSN) ; Meyer, M. M ; O'Hair, R. A. J ; Fattahi, A ; Schmidt, J ; Kass, S. R ; Sharif University of Technology
Elsevier B.V
2017
Abstract
Electrospray ionization of 2,6-naphthalenedicarboxylic acid readily affords its doubly deprotonated dicarboxylate dianion (12−). This species clusters with background water and added alcohols in an ion trap at ∼10−3 Torr. Sequential solvation is observed to afford mono and dicoordinated ions. Surprisingly, the latter cluster (12−• 2TFE) is protonated by 2,2,2-trifluoroethanol (TFE) whereas 12−and 12−• TFE are not even though ΔH°acid(TFE) = 361.7 ± 2.5 kcal mol−1 (as given in the NIST website at http://webbook.nist.gov) and the B3LYP/6-31+G(d,p) proton affinities are 384.7 (12−), 377.6 (12−• TFE), and 362.7 (12−• 2TFE) kcal mol−1. That is, only the weakest base in this series, and the dianion...